High Heels Training Stories

211,551 results
Orientation
Length
Source
Infinite Scroll

Silver Moon: Bk. 02 Ch. 13

by maxd01 on Sep 13, 2017
NonHuman

Even with his mate glaring down at him, Dan had an innocent expression on his face. "Why would I do something like that love? I know you hate rats even if Amarish likes them and thinks of them as large mice. I will be more than happy to look into this for you if you want." With every fiber of his being he was trying to come across as wanting to be helpful an...

Rebecca's Dilemma

by CeeeEsss on Sep 17, 2017
Loving Wives

Three young women looking for a fun night, walked into the only drinking establishment, within a half hour's drive, where they could buy a beer. One faction of residents of the small farming community had repeatedly defeated the other faction's attempts to turn the county from 'dry' to 'wet'. Adjacent to the dry county was another county that also did not...

The Boys in Blue Ch. 17

by RobinLane on Sep 13, 2017
Novels and Novellas

After reporting to Alan and having a chat, he went to his office, groaning at the sight of the stack of folders on his desk, after three hours, and he had hardly made a dent in the pile. He left for the Officers Mess finding the seven pilots sitting around a couple of tables, after putting up with the bawdy remarks concerning honeymoons, he turned to Tim. "...

Horny Old Maid

by alanc on Sep 11, 2017
Mature

After recently moving into a new block of flats I was still in the process of meeting my new neighbours whenever I saw them in the lobby, lift, laundry room etc. One day after returning home from another long day at work I finally bumped into the lady who lived across the hall, just as she was coming out of her own apartment. She introduced herself as Jean a...

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

Weekend Games Ch. 02

by SissyAndi on Sep 16, 2017
Transsexuals & Crossdressers

I relived the things that had happened between Tammy and myself over and over. I was not sure how Tammy would act around me after what we had done that first weekend but when I picked her up for work the next Wednesday she didn't mention it and acted like nothing had happened. The week dragged on and I would begin to think it was all part of my active imag...

F.I.L.W.A.H.M Ch. 02

by Meow5meow on Apr 4, 2018
Celebrities & Fan Fiction

Ch 2. The First Interview I pulled into Arkham parking lot ten minutes early for work, something I did rarely. I got out of the car with a brand new notebook, and a piping hot cup of coffee. My heels clicked on the wet pavement as I made my way towards the sliding doors of the main entrance. I wore red heels with dark blue jeans and a light pink turtleneck....

Cuckbitch Pt. 04: The Party

by Satin_Dani on Dec 2, 2019
Transgender & Crossdressers

Lucy was getting stationed overseas. More than anything we realized it would suck as we couldn't hang out anymore. As for myself and our naughty adventures, I realized that it would probably decline, especially since her operational tempo would probably increase, meaning her time would be limited and since she would be on the other side of the world, timing...

First Time Sharing My Wife

by GBM1966 on Feb 11, 2019
Loving Wives

This is my first time posting a story on Literotica. Not a great writer, sorry for any grammar mistakes. This was a fantasy for a long time but came true about 12 years ago. My wife and I are now 52 years old and have gotten together a few times over the years with my best friend. My wife, Becky and I have pillowed talked about sharing her with another man...

Toilet Training Elizabeth

by lesliejones on Sep 25, 2017
Fetish

For my darling Megs * Kendall stood up before the assembled ladies of her exclusive women's luncheon club and pointed her finger at her daughter-in-law Elizabeth to join her on the stage. Kendall was enjoying herself immensely and looked forward to this little presentation. Meanwhile her daughter-in-law, at 25 only a few years younger than her dominating m...